NP-MRD: Showing NP-Card for n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide (NP0186395)

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Record Information

Version

2.0

Created at

2022-09-04 02:14:03 UTC

Updated at

2022-09-04 02:14:03 UTC

NP-MRD ID

NP0186395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide

Description

Saracodine belongs to the class of organic compounds known as azasteroids and derivatives. These are steroid derivatives in which one carbon atom in the steroidal skeleton has been substituted with a nitrogen atom. n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide is found in Sarcococca coriacea and Sarcococca saligna. n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide was first documented in 2005 (PMID: 16431389). Based on a literature review a small amount of articles have been published on Saracodine (PMID: 31584741) (PMID: 26093268) (PMID: 29454755) (PMID: 15789498).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204142D          

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M  END

     RDKit          3D

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  Mrv1652309042204142D          

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M  END
> <DATABASE_ID>
NP0186395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C)N(C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H46N2O/c1-17(28(7)18(2)29)22-10-11-23-21-9-8-19-16-20(27(5)6)12-14-25(19,3)24(21)13-15-26(22,23)4/h17,19-24H,8-16H2,1-7H3/t17-,19-,20+,21-,22+,23-,24-,25-,26+/m0/s1

> <INCHI_KEY>
VPOYXIYUORUTSW-CVKOZZCDSA-N

> <FORMULA>
C26H46N2O

> <MOLECULAR_WEIGHT>
402.667

> <EXACT_MASS>
402.361014109

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
50.48067880675019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1S)-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-(dimethylamino)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethyl]-N-methylacetamide

> <JCHEM_LOGP>
4.4238245386666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.200357773519848

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
121.65959999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S)-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-(dimethylamino)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethyl]-N-methylacetamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.892  -8.295   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.257  -5.652   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      16.362  -3.071   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      16.886  -1.622   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    8   11   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₆N₂O

Average Mass

402.6670 Da

Monoisotopic Mass

402.36101 Da

IUPAC Name

N-[(1S)-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-(dimethylamino)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethyl]-N-methylacetamide

Traditional Name

N-[(1S)-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-(dimethylamino)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethyl]-N-methylacetamide

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C)N(C)C(C)=O

InChI Identifier

InChI=1S/C26H46N2O/c1-17(28(7)18(2)29)22-10-11-23-21-9-8-19-16-20(27(5)6)12-14-25(19,3)24(21)13-15-26(22,23)4/h17,19-24H,8-16H2,1-7H3/t17-,19-,20+,21-,22+,23-,24-,25-,26+/m0/s1

InChI Key

VPOYXIYUORUTSW-CVKOZZCDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sarcococca coriacea	LOTUS Database	35616633
Sarcococca saligna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azasteroids and derivatives. These are steroid derivatives in which one carbon atom in the steroidal skeleton has been substituted with a nitrogen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Azasteroids and derivatives

Direct Parent

Azasteroids and derivatives

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
Azasteroid
Alkaloid or derivatives
Tertiary carboxylic acid amide
Acetamide
Tertiary amine
Carboxamide group
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Amine
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.42	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.66 m³·mol⁻¹	ChemAxon
Polarizability	50.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57570388

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12315307

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ali A, Jan NU, Ali S, Ahmad B, Ali A, Samrana S, Jahan A, Ali H, Khan IA, Rahim H, Ali I, Kifayatullah M, Amin F: Steroidal alkaloids efficient aromatase inhibitors with potential for the treatment of postmenopausal breast cancer. Chem Biol Drug Des. 2020 Feb;95(2):233-239. doi: 10.1111/cbdd.13635. Epub 2019 Nov 10. [PubMed:31584741 ]
Ali H, Musharraf SG, Iqbal N, Adhikari A, Abdalla OM, Ahmed Mesaik M, Kabir N: Immunosuppressive and hepatoprotective potential of Sarcococca saligna and its biomarker components. Int Immunopharmacol. 2015 Sep;28(1):235-43. doi: 10.1016/j.intimp.2015.06.009. Epub 2015 Jun 17. [PubMed:26093268 ]
Naeem I, Anwar R, Khan TM: Anti-bacterial alkaloids of Saracococca saligna. Pak J Pharm Sci. 2005 Apr;18(2):3-5. [PubMed:16431389 ]
Ullah Jan N, Ali A, Ahmad B, Iqbal N, Adhikari A, Inayat-Ur-Rehman, Ali A, Ali S, Jahan A, Ali H, Ali I, Ullah A, Musharraf SG: Evaluation of antidiabetic potential of steroidal alkaloid of Sarcococca saligna. Biomed Pharmacother. 2018 Apr;100:461-466. doi: 10.1016/j.biopha.2018.01.008. Epub 2018 Feb 15. [PubMed:29454755 ]
Giliani AU, Ghayur MN, Khalid A, Zaheer-ul-Haq, Choudhary MI, Atta-ur-Rahman: Presence of antispasmodic, antidiarrheal, antisecretory, calcium antagonist and acetylcholinesterase inhibitory steroidal alkaloids in Sarcococca saligna. Planta Med. 2005 Feb;71(2):120-5. doi: 10.1055/s-2005-837777. [PubMed:15789498 ]
LOTUS database [Link]

Showing NP-Card for n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide (NP0186395)

MOL for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

3D MOL for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

3D SDF for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

3D-SDF for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

PDB for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

3D PDB for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

SMILES for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

INCHI for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

Structure for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)

3D Structure for NP0186395 (n-[(1s)-1-[(1s,3as,3br,5as,7r,9as,9bs,11as)-7-(dimethylamino)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl]-n-methylacetamide)